In this conceptual document, I present a critical model of mentoring that suggests that mentee professional identity influences how role modeling occurs and, as a consequence, shapes mentoring learning outcomes. The model suggests that the role modeling function of mentoring might not always be beneficial and that the degree to which a mentee has a well-defined professional identity will affect when role modeling supports personal learning, specifically, the outcome of personal adaptability. Although reliance on traditional, exchange-based modeling and emulation are helpful as mentees work to establish their professional identities, it is expected to produce less favorable and potentially detrimental learning outcomes as mentees begin to develop more well-established self-identities. Accordingly, this article contributes to the extant discussion on mentoring to suggest that mentoring relationships characterized by mutuality produce a path that better suits the learning needs of those mentees whose professional identities are better defined. The model is delimited according to phases of the mentoring relationship and asserts that this proposed effect is likely to become salient in the cultivation phase. I derive from these assertions a series of testable propositions that set the stage for future research and outline steps that mentor models may consider to meet their mentees' learning needs through authentic mentoring practices.